Introduction

Rogues are the quintessential Face, Scout and Striker. Sneak Attack allows them to do a huge pile of damage in a single attack, and their pile of skills allows them to easily handle locks, traps, guards, and many other challenges. While a party can function just fine without a Rogue, it’s hard to compete with the sheer number of important skill and tool proficiencies offered by the Rogue.

Rogues typically split into melee or ranged builds, though the universal efficacy of Dexterity makes it easy for many rogues to switch between the two. Melee Rogues frequently go for two-weapon fighting because it provides a second chance to score Sneak Attack, and hit-and-run tactics enabled by Cunning Action are great way to get into melee to attack before retreating behind your party.

Ranged rogues typically rely on sniping, which is also enabled by Cunning Action due to the ability to hide as a Bonus Action. Hiding after each attack using Cunning Action is reliable and effective, though it can be very static and repetitive. Rogue subclasses expand upon those tactical options, but in many cases these staple tactics remain crucial to the class’s function.

After reading this handbook, I encourage you to read our Rogue Races Breakdown, Rogue Subclass Breakdown, and Rogue Spells Breakdown if you plan to play an Arcane Trickster.

Table of Contents

Disclaimer

RPGBOT uses the color coding scheme which has become common among Pathfinder build handbooks, which is simple to understand and easy to read at a glance.

  • Red: Bad, useless options, or options which are extremely situational. Nearly never useful.
  • Orange: OK options, or useful options that only apply in rare circumstances. Useful sometimes.
  • Green: Good options. Useful often.
  • Blue: Fantastic options, often essential to the function of your character. Useful very frequently.

We will not include 3rd-party content, including content from DMs Guild, in handbooks for official content because we can’t assume that your game will allow 3rd-party content or homebrew. We also won’t cover Unearthed Arcana content because it’s not finalized, and we can’t guarantee that it will be available to you in your games.

The advice offered below is based on the current State of the Character Optimization Meta as of when the article was last updated. Keep in mind that the state of the meta periodically changes as new source materials are released and this article will be updating accordingly as time allows.

RPGBOT is unofficial Fan Content permitted under the Fan Content Policy. Not approved/endorsed by Wizards. Portions of the materials used are property of Wizards of the Coast. ©Wizards of the Coast LLC.

Rogue Class Features

Optional Class Features are detailed below under Optional Class Features.

Hit Points: 1d8 hit points is dangerous if you go into melee alone, so be sure to have a nice tanky ally nearby and a healer waiting in the wings.

Saves: Dexterity saves will protect you from things like fireballs, and Intelligence saves also exist I suppose. Evasion further improves your Dexterity saves.

Proficiencies: Rogues get all of the weapons they need to get by, but thieves’ tools, and a fantastic four skills.

Expertise: Rogues are truly the master of skills. Pick skills which fit the theme and style of your campaign and your character well.

Sneak Attack: Sneak Attack is the source of most of the Rogue’s damage, and should define your combat tactics. You can only use it once per turn, which is disappointing for two-weapon fighting builds, but once per turn is plenty. Also note that it’s per turn, not per round, so you can potentially use your reaction to Sneak Attack a second time in a round.

Thieves’ Cant: Really only matters for flavor.

Cunning Action: This is a fantastic option for bringing your Sneak Attack into play. Archers can use Hide to stay hidden between attacks, and melee Rogues can use Dash and Disengage to move around the battlefield safely and quickly.

Roguish Archetype: Rogue subclasses are briefly summarized below. See my Rogue Subclasses Breakdown for help selecting your subclass.

  • Arcane Trickster: Use illusions and enchantments to confuse and outsmart your foes.
  • Assassin: Masters of infiltration, disguise, and dealing high-damage sneak attacks at the beginning of combat.
  • Inquisitive: Masters of Insight and Investigation, the Inquisitive is hard to surprise or fool, and they can use their keen insight to allow them to Sneak Attack foes more easily than most rogues.
  • Phantom: Speak to the spirits of the dead and use their knowledge to empower your attacks and your skills.
  • Mastermind: Masters of planning and tactics, the Mastermind can use the Help action to great effect in combat, and can gain insights about other creatures outside of combat by studying them at length.
  • Scout: Adept skirmishers and ambushers, scouts are fast and difficult to pin down in combat, and move about quickly on the battlefield.
  • Soulknife: Use psionic power to create deadly psychic blades in combat.
  • Swashbuckler: Charismatic master duelists, swashbucklers use their Charisma in unique ways both in and out of combat, and are masters at engaging foes one-on-one.
  • Thief: The iconic rogue, the Thief is a master of using tools and items (including magic items) to overcome challenges quickly.

Uncanny Dodge: If you only draw a handful of attacks this can prevent a huge amount of damage.

Evasion: Between this and uncanny dodge you are very durable.

Reliable Talent: This is especially nice for your Expertise skills, and it’s great motivation to pick up the Skilled feat.

Blindsense: Locating invisible creatures can be very hard, and even if you can’t hit them easily it goes a long way to know where they are standing.

Slippery Mind: Your Wisdom probably isn ‘t great, but at this level your Proficiency Bonus is big enough that this goes a long way.

Elusive: Between this, Uncanny Dodge, and Evasion you are very difficult to kill.

Stroke of Luck: Essential when the chips are down and you can’t afford to fail.

Optional Class Features

Introduced in Tasha’s Cauldron of Everything, Optional Class Features offer ways to add additional features or replace existing ones. These rules are optional, and you should not assume that your DM will allow these features without consulting them first.

Assessments and suggestions for specific Optional Class Features are presented here, but for more information on handling Optional Class Features in general, see my Practical Guide to Optional Class Features.

Steady Aim (Addition): Nowhere to hide? Nowhere to run? No shenanigans to get easy access to Sneak Attack? Steady Aim is your answer. It’s not especially exciting, but it’s incredibly effective, and provides a way for rogues to achieve Sneak Attack in situations where they might otherwise struggle to do so.

I recommend allowing Steady Aim on all single-class rogues who take subclasses that I rate orange or red, but you might also allow it for new players who are acclimating to 5e’s rules, especially if they struggle to keep track of the conditions which allow them to deliver sneak attacks. Delivering Sneak Attack is 5th edition is really easy in most situations, and having situations where the rogue can’t manage sneak attack is part of what balances the Rogue’s consistently high damage output. For a new player (or players who struggle with game mechanics) this can be a helpful crutch, but for experienced players who are comfortable with the rules, this is basically an on-switch for easy mode.

You do give up the ability to move under your own power for the turn in which you use Steady Aim, but that conveniently doesn’t apply to mounts or to a broom of flying, so abuse cases are both abundant and easy to access. If you’re asking yourself if you or someone in your game is experienced enough with the game that you don’t need Steady Aim, I recommend this as a barometer: If the player in question knows the game well enough to think of a horse as an abuse case, that player probably doesn’t need Steady Aim.

Rogue Ability Scores

Dexterity is key for any Rogue, and Intelligence is important for Arcane Tricksters, but your need for Wisdom and Charisma depend largely on your choice of skills and role in the party.

Str: Typically your dump stat. Nothing that a typical Rogue does uses Strength. However, you’re not forced to use Dexterity to make Sneak Attacks so long as you use a suitable weapon, so Strength-based rogues are technically possible. It’s usually a bad idea, but it is absolutely possible.

Dex: Rogues run on Dexterity. They add to you skills, your tools, your attacks, your damage, your AC, and your best save.

Con: Hit points are always important, especially for melee Rogues.

Int: Arcane Tricksters need Intelligence for their spells, but other Rogues only need it for Investigation.

Wis: Helpful for Insight and Perception, but otherwise useless. Inquisitives will want a bit more to power Unerring Eye, but Expertise will outweight your ability modifier anyway so you don’t need much.

Cha: Rogues make a great Face, and you can’t be a Face without Charisma.

Most RoguesArcane Trickster
Point BuyStandard ArrayPoint BuyStandard Array
Str8888
Dex15151515
Con14141413
Int11101414
Wis12131012
Cha12121010

Rogue Races

Dexterity bonuses are critical, and Darkvision is fantastic for sneaking around in the dark. Size doesn’t matter since Rogues don’t use heavy weapons. That sets a very low bar for races that work for the Rogue, so there’s a lot of room to look for other benefits. Access to better weapons like heavy crossbows, racial traits like flight, innate spellcasting, and damage resistances can all be excellent assets and with such simple requirements you have lots of room to explore racial traits which go beyond ability score increases.

Note that setting-specific races like the Changeling and the Satyr are addressed in setting-specific sections, below.

For more, see our Rogue Races Breakdown.

For a classic rogue feel, consider the Lightfoot Halfling. For a highly-skilled rogue, consider the Half-Elf or the Kenku. For a high-damage melee rogue, consider the High Elf. For a ranged rogue, consider the Fairy or the Owlin.

Rogue Skills

  • Acrobatics (Dex): Very situational.
  • Athletics (Str): Rogues don’t really do anything that requires Athletics. Thieves might want it for climbing, but even that is very infrequent.
  • Deception (Cha): Important for a Face.
  • Insight (Wis): Important for a Face.
  • Intimidation (Cha): Important for a Face.
  • Investigation (Int): Very helpful, but not as important as Perception.
  • Perception (Wis): Perception is by far the most important skill in the game, and it’s important that several characters in the party have it.
  • Performance (Cha): Performance is for Bards.
  • Persuasion (Cha): Essential for a Face.
  • Sleight of Hand (Dex): Sleight of Hand is very thematic for many Rogues, but it’s not very useful.
  • Stealth (Dex): A Rogue without Stealth is a very strange Rogue.

Rogue Backgrounds

This section does not address every published background, as doing so would result in an ever-growing list of options which don’t cater to the class. Instead, this section will cover the options which I think work especially well for the class, or which might be tempting but poor choices. Racial feats are discussed in the Races section, above.

Rogues can do a lot, but they also need a lot of skills to do it all. Look for backgrounds which fill in proficiencies which are already on the Rogue skill list but which you couldn’t get with yoour choice of two skills.

If you’re having trouble deciding, here are some suggestions:

  • AcolytePHB: Insight and Religion can be decent options for a Rogue with the right abilities, and extra languages are helpful for a Face.
  • CharlatanPHB: Two Rogue skills and two tool kits.
  • City WatchSCAG: Athletics doesn’t do much for Rogues, but Insight and free languages are great for a Face.
  • Cloistered ScholarSCAG: Two knowledge skills and two language can be excellent additions to a Face with decent Intelligence.
  • CourtierSCAG: Perfect for a Face.
  • CriminalPHB: Two important Rogue skills, and two tool kits. You already get Thieves’ Tools proficiency as a Rogue, so you can replace Thieves’ Tools with another proficiency of the same type. I recommend Poisoner’s Kit.
  • EntertainerPHB: Disguise Kit proficiency is really the only interesting piece.
  • Faction AgentSCAG: Fantastic for a Face, and it allows you to fill in a social skill which you couldn’t get elsewhere.
  • Far TravelerSCAG: Two excellent skills for a Rogue, a bonus language, and proficiency with an item that you’ll probably never use.
  • Guild ArtisanPHB: Two important skills for any Face, but the tool proficiency isn’t very helpful.
  • InheritorSCAG: You can’t really use Survival, but the rest is decent. Far Traveler provides similar options with better skills.
  • Mercenary VeteranSCAG: Athletics is occasionally useful for Rogues, and any face needs Persuasion.
  • NoblePHB: A good choice for a Face. History is decent if you have a bit of Intelligence to back it up.
  • SagePHB: An Arcane Trickster might have enough Intelligence to justify two knowledge skills, and the extra languages are nice for a Face.
  • Urban Bounty HunterSCAG: Basically two additional skill choices from the Rogue class skills, plus some tool proficiencies, including the ever-important Thieve’s Tools.
  • UrchinPHB: Two important Rogue skills, and two tool kits. You already get Thieves’ Tools proficiency as a Rogue, so you can replace Thieves’ Tools with another proficiency of the same type. I recommend Poisoner’s Kit.
  • Waterdavian NobleSCAG: Potentially good for a Face with decent Intelligence.

Rogue Feats

This section does not address every published feat, as doing so would result in an ever-growing list of options which don’t cater to the class. Instead, this section will cover feats which I think work especially well for the class or which might be tempting but poor choices.

  • AlertPHB: Going first is great for Rogues, especially Assassins.
  • ActorPHB: Complements the Assassin’s disguise and infiltration abilities very nicely.
  • Crossbow ExpertPHB: If you’re built to fight at range, Crossbow Expert is tempting. Allowing an additional crossbow attack as a bonus action gives you a backup option if you fail to deliver a Sneak Attack on your first attack, and unlike two-weapon fighting you get to apply your ability modifier to damage with the additional attack. However, you can accomplish the same thing by throwing daggers (though your range is considerably reduced). The ability to use ranged weapons while adjacent to enemies is also tempting, but that’s what Cunning Action is for.
  • Defensive DuelistPHB: Very tempting for melee Rogues, but Uncanny Dodge also uses your reaction, and fills roughly the same function.
  • Dual WielderPHB: The best case scenario for this feat is upgrading from two short swords to two rapiers, and the tiny bit of extra damage is hardly worth a feat. The +1 AC is nice too, but raising your Dexterity will get you the same AC and damage boosts, plus it will improve your other crucial stats. Two-weapon fighting should be primarily considered a way to get an extra sneak attack rather than a go-to source of damage output
  • Dungeon DelverPHB: Handling traps and secret doors frequently falls to the Rogue, and with the Rogue’s skills this can make you extremely effective in a dungeon-heavy campaign.
  • DurablePHB: Leave this for your party’s front line.
  • Eldritch AdeptTCoE: If you don’t have Darkvision from your racial traits, the Devil’s Sight invocation is a great way to get it. Unfortunately you do need some spellcasting to qualify, so this is only available to the Arcane Trickster. If you want to consider other invocations, see my Warlock Eldritch Invocation Breakdown.
  • Elemental AdeptPHB: Offensive spells (with the exception of Green-Flame Blade) aren’t a good option for Arcane Tricksters because you can’t apply Sneak Attack, and if you’re worried about damage resistance you can use Booming Blade instead since almost nothing resists sonic damage.
  • Fey TouchedTCoE: Tempting for many rogues, especially arcane tricksters. Misty Step is extremely useful in a variety of situations, and the leveled spells can add some utility options which are hard to replicate without magic. Avoid Hex and Hunter’s Mark since the Rogue makes so few attacks, but consider Bless and Gift of Alacrity.

    For more advice on Fey Touched, see my Spellcasting Feats Breakdown.

  • Fighting InitiateTCoE: If you’re relying on bows, Fighting Style (Archery) can be a huge improvement to your damage output. Blind Fighting may be helpful since the Rogue doesn’t have a built-in way to handle invisible foes, and blindsight conveniently allows you to fight within the area of magical darkness or an Eversmoking Bottle so combining the two is an easy way to get the upper hand in combat. Superior Technique gets you a Battle Master maneuver and a Superiority Die, but it’s one die per short rest, which isn’t worth a feat no matter how good the Riposte maneuver is for the Rogue.
  • GunnerTCoE: Upgrading from a hand crossbow to a musket can be a minor damage boost, but getting proficiency with longbows from your race is less costly and arguably more effective since you’re not giving away your position by shooting a gun. Bows aren’t totally silent, but they’re nowhere near as loud as a firearm.
  • HealerPHB: The best use case for this feat is the Thief. Thanks to Fast Hands, you can use a Healer’s Kit as a Bonus Action, allowing you to revive dying allies and retore a small amount of hit points. Of course, you can do the same thing with a Potion of Healing as an Action, so it’s a question of how often you need to come to the rescue in a game where Healing Word exists. In fact, you might just take Magic Initiate with Bard, Cleric, or Druid to get Healing Word for the rare times where your party’s spellcasters can’t do the job because you’ll also get two cantrips and because Healing Word works at range.
  • Inspiring LeaderPHB: A Rogue with good enough Charisma to use this feat is an excellent choice. Temporary hit points hugely reduce your need for magical healing, and there is little reason not to use this before every fight.
  • Magic InitiatePHB: The Sword Coast Adventurer’s Guide introduced Booming Blade and Green-Flame Blade, both of which are an Action and allow you to make a melee attack with a weapon, thereby allowing you to use them in conjunction with Sneak Attack. Since Rogues never get Extra Attack, these cantrips can be a significant boost to both damage and utility. Booming Blade is a great way to discourage enemies from following you after you hit them and using Cunning Action to Disengage, and Green-Flame Blade grants some easy bonus damage, plus it allows you to damage a second target, which is particularly nice since Rogues are so bad at handling crowds of enemies. You may also consider options like True Strike to get easy advantage (it only has somatic components, so you can easily use it while hiding) if you’re not using the Steady Aim Optional Class Feature.

    Unless you’re an Arcane Trickster, the 1st-level spell should probably be a long-duration buff like Mage Armor (don’t do it; real armor is better) or a reliable utility option. Find Familiar is tempting so that you can get an owl to fly in and out of combat taking the Help action, but you get to cast the spell daily so you may want something that you’ll definitely use on a daily basis so you don’t feel like your under-using the feat.

    For more advice on Magic Initiate, see my Spellcasting Feats Breakdown.

  • Martial AdeptPHB: One maneuver per short rest isn’t enough to justify this for the Rogue.
  • Metamagic AdeptTCoE: Powerful, but the Arcane Trickster doesn’t get enough spellcasting to make this an easy choice. For advice on Metamagic Adept, see my Sorcerer Metamagic Breakdown.
  • MobilePHB: Hit-and-run tactics are great for melee Rogues, but moving out of a creatures threatened area is normally dangerous. This allows you to run in, attack, then run away safely. You can use Cunning Action to Dash, allowing you to move considerably further in one round, and possibly to hide behind difficult terrain.
  • Moderately ArmoredPHB: You need to be improving your Dexterity enough that medium armor shouldn’t be a good option.
  • ObservantPHB: Potentially helpful if no one else in your party has Investigation or Perception, but probably overkill. If you really need this, use Expertise to improve your skills.
  • PiercerTCoE: Easy to fit into your build, and with Sneak Attack you’ll have a die which rolls low almost every turn so you’ll benefit from the reroll mechanic constantly. The critical hit mechanic doesn’t matter much since rogues get by on small damage dice, and with so few attacks critical hits will be infrequent for most rogues (assassins are an exception).
  • PoisonerTCoE: If you have a ton of money and nothing to spend it on, this is a great way to turn it into damage output. The poison provided by the feat is both inexpensive compared to other poisons (which are prohibitively expensive) and deals a reasonable amount of damage plus the Poisoned condition. Unfortunately, the DC 14 Constitution save will be unreliable against many enemies, so you’ll need to be picky about when to use poisons rather than using them in every encounter. Because applying a poison requires your Bonus Action, you’ll need to juggle poisoning your weapons with your other Bonus Action options like Cunning Action. Fighting at range will make this action management simpler, but missing with an arrow or a crossbow bolt likely wastes the dose of poison, so you’re trading one problem for another.
  • ResilientPHB: Constitution saves might be helpful, but other saves aren’t common enough to justify taking this over Lucky.
  • Ritual CasterPHB: A great way for Arcane Tricksters to improve their utility options if your party lacks dedicated spellcasters. Find Familiar is a fantastic option because your familiar can take the Help action to grant you Advantage on your attacks.
  • Savage AttackerPHB: This is a bad feat. The largest damage die (d12), yields an average of 2 extra damage per turn, and generally the Rogue’s biggest damage die is only 1d8.
  • SentinelPHB: Sentinel can be a great way to get opportunity attacks, thereby giving you more opportunities to apply Sneak Attack. However, you may find it difficult to apply Sneak Attack because you can’t guarantee positioning or Advantage on other creatures’ turns. An enemy could easy move around within your reach until it is no longer adjacent to one of your allies before leaving your threatened area, thereby avoiding the bonus damage from Sneak Attack. Swashbucklers will be able to make best use of this part of the feat since their positioning requirements are so easily met. It’s also unlikely that enemies will attack your allies while you’re in reach because rogues are relatively soft targets. With light armor and 1d8 hit points, you’re among the most frail melee characters. However, if you have a paladin in the party you can capitalize on options like Compelled Duel.
  • Shadow TouchedTCoE: An Arcane Trickster can already replicate the interesting parts of Shadow Touched.

    For more advice on Shadow Touched, see my Spellcasting Feats Breakdown.

  • SharpshooterPHB: Absolutely fantastic for archer Rogues. Combined with Sneak Attack, you can do some truly crazy damage. Just be sure that you have Advantage, or you’re going to miss frequently, and hitting so that you an deliver Sneak Attack is more important than the damage boost from Sharpshooter. If the Steady Aim Optional Class Feature is an option, combining it with Sharpshooter is very effective.
  • Skill ExpertTCoE: You probably don’t need more skills or more expertise, but it certainly doesn’t hurt.
  • SkilledPHB: With Reliable Talent you can reliably use any skill you know, even with a mediocre ability score.
  • SkulkerPHB: Very helpful for archer Rogues who like to rely on sniping.
  • Spell SniperPHB: You can’t use Sneak Attack with spell attacks.
  • TelekineticTCoE: It may be difficult to juggle your Bonus Action between this and things like Cunning Action, but it offers and easy way to get out of grapples without spending your Action to try to escape. Telekinetic is especially worthwhile for the Arcane Trickster since it removes the spellcasting components, allowing you to use it totally undetected.
  • TelepathicTCoE: Unlike many sources of telepathy, including those offered by some races, this telepathy still uses languages, so the benefits are minimally appealing even for a Face. You do get to increase a mental ability score, which reduces the cost of the feat, but the benefits are primarily the ability to communicate while being stealthy.
  • War CasterPHB: Tempting for Arcane Tricksters thanks to Green-Flame Blade and Booming Blade, but definitely not necessary.

Rogue Weapons

  • Crossbow, Hand: A decent ranged weapon, but it doesn’t do anything that you can’t do with a light crossbow.
  • Crossbow, Light: The go-to ranged weapon. The same range as a short bow with a better damage die. The reload property doesn’t matter since rogues don’t get Extra Attack.
  • Dagger: Great for Two-weapon fighting, and you can throw them if you need to, but the Short Sword has a slightly larger damage die.
  • Longsword: I’m not sure why Rogues get proficiency with long swords.
  • Rapier: Your best bet for single-weapon melee.
  • Shortsword: Ideal for Two-weapon fighting. Comparable to daggers, but you can’t throw them
  • Short bow: Light crossbow is strictly better.

Rogue Armor

  • Leather: Free starting armor for light armor users. Upgrade as soon as you can afford it.
  • Studded Leather: Your permanent armor.

Multiclassing

This section briefly details some obvious and enticing multiclass options, but doesn’t fully explore the broad range of multiclassing combinations. For more on multiclassing, see my Practical Guide to Multiclassing.

  • Artificer: The Artificer is an interesting option for many rogues. The Artificer’s cantrips include melee cantrips like Booming Blade, and their spellcasting includes a combination of buffs and healing options which can add a lot of utility. Two levels gets you access to Infusions, including powerful options like Enhanced Defence and replicate Magic Item so that you can get Goggles of Night if your race doesn’t have Darkvision. Three levels gets you a subclass, and the Armorer subclass’s Infiltrator Armor offers perpetual advantage on Stealth checks as well as a powerful ranged attack option which you can choose to use with Dexterity and which works with Sneak Attack since it’s a weapon attack. If magic items like a Cloak of Elvenkind are available in your game this is less appealing, but in games where that’s not an option the Artificer is very tempting.
  • Barbarian: Reckless Attack is very tempting because it provides a guaranteed means of gaining Advantage and dramatically improves your probability of applying Sneak Attack. However, on a class as frail as the Rogue it can be dangerous to grant Advantage against yourself and there are plenty of other ways to gain reliable access to Advantage and Sneak Attack. You gain proficiency in shields and Unarmored Defense, which can both potentially raise your AC to help offset Reckless Attack, but then you need high scores in all of Str/Dex/Don.

    You need to make reckless attacks using Strength rather than Dexterity, which is a hard way to build a rogue most of the time. At level 18 Elusive negates the downside of Reckless Attack, but building a character around one trick which won’t work until level 20 almost never pays off since so few campaigns reach high levels.

  • Bard: Want more Expertise? Consider College of Eloquence, and three levels gets you Expertise in two more skills and a floor on your d20 rolls for Depection and Persuasion checks. Perfect for a Face build.
  • Fighter: Fighting Style goes a very long way for the Rogue if you go for Archery, but Two-Weapon Fighting is a trap. Adding 2-5 damage (depending on your Dexterity) really won’t matter compared to your Sneak Attack damage, so stick to Rogue for Two-Weapon Fighting builds. Swashbucklers might consider the Fencing style and pick up a shield (and possibly even medium armor) so that they can make good use of Panache. The +2 damage outpaces the 1.75 average Sneak Attack damage you get per Rogue level, so a single level won’t cut into your damage output.

    If you can suffer three levels of Fighter, the Battle Master offer some useful options. Riposte allows you a reliable way to get an extra Sneak Attack per round (remember that Sneak Attack is once per turn), especially for swashbucklers who can apply Sneak Attack easily in melee unassisted. Feinting Attack also provides Advantage, allowing for easy Sneak Attack during your turn. However, those options depend on Superiority dice, so your usage is severely limited and you’ll need to manage your pool of dice carefully.

    If you’re going for a Strength-based build, starting with 1 level in Fighter gets you heavy armor in exchange for the Rogue’s additional skill and tool proficiencies. If you don’t need the extra proficiencies, that might be a fine trade.

  • Monk: Way of the Shadow is a massively tempting option for Rogues, but the 3rd-level benefit isn’t worth three levels, and the 6th-level benefit costs you too much to obtain.
  • Ranger: 2 levels gets you a Fighting Style and access to Hunter’s Mark, which makes Two-Weapon Fighting more viable (though still not necessarily great). Three levels gets you a a subclass, and the Hunter can select Giant Killer as their 3rd-level ability. Giant Killer allows you an attack as a Reaction, offering a way to get an extra Sneak Attack per round every round without a usage limitation. If they hit you, use Uncanny Dodge. If they miss you, use Giant Killer. That extra attack will easily make up for the lost Sneak Attack damage progression.
  • Sorcerer: 1 level of Draconic Bloodline gets you 13+Dex AC (beating any non-magical light armor by at least 1), and a bit of spellcasting. If you stick to spells which don’t require spell attacks or saving throws (utility options and options like Booming Blade), you could benefit from this class dip without more than the 13 Charisma required to multiclass into Sorcerer. For your leveled spells options like Absorb Elements and Shield are tempting, but don’t feel locked into those options since the Rogue gets Uncanny Dodge and Evasion which provide much of the same functions.
  • Warlock: Sadly your can’t deliver Sneak Attack with Eldritch Blast, but there’s still plenty here to make a Rogue+Warlock enticing. For a high-Charisma build, a single level of Hexblade will allow you to use Charisma for attacks, allowing you to improve your social skills and your combat abilities at the same time. 3rd level gets you Pact Boon, and if you select Pact of the Blade you can retrain your Eldritch Invocation gained at 2nd level to get Improved Pact Weapon (+1 to attacks and damage!).
  • Wizard: One level gets you some spellcasting, including ritual casting and access to great options like Booming Blade and Find Familiar. Two levels to pick up the Bladesinging tradition offers some excellent options for melee Rogues, including proficiency in a one-handed melee weapon like the Whip. Bladesong grants a nice AC boost (especially for Arcane Tricksters) and some other great benefits, and access to Wizard spells removes the need for the Magic Initiate feat. Since you have more spell options than Magic Initiate provides, pick up Find Familiar and have your familiar use the Help action to grant you Advantage (and therefore Sneak Attack) on your attacks.

Rogue Magic Items

Common Magic Items

  • Clockwork AmuletXGtE: Only works once per day, but in many encounters a guaranteed 10 on attack roll will guarantee a hit (Players will hit an average CR-appropriate enemy’s AC on an 8 or better. See my article on The Fundamental Math of Character Optimization.) For high-value attacks (any Sneak Attack, basically), that can be great insurance. Even better: you don’t need to attune this, so you can rotate through a stack of them if your DM is somehow crazy enough to let you get away with it.
  • Horn of Silent AlarmXGtE: A helpful tool for any Scout, the effect allows you to communicate with your allies (albeit in very simple fashion) at a distance without giving away your position and without relying on more complicated and expensive options like telepathy. Use one blare to alert your party that you’re in danger, and establish a meaning for two or more blares before you go off scouting. Example: Two blares means come to me, but be cautious. Three blares means come get me, but the way is safe.
  • Masquerade TattooTCoE: Disguise Self once per day. Basically a cheaper Hat of Disguises. You won’t be able to change your disguise, but it’s still fantastically useful for a Common item.
  • Moon-Touched SwordXGtE: This solves two problems for the martial characters. First, the sword glows almost as brightly as a torch, allowing you to see in dark places without devoting a hand to a torch and without asking your allies to cast light or something. Second, and more important, it allows you to overcome damage resistance to non-magic attacks. Resistances like this are common as you gain levels, and the Moon-Touched Sword is an inexpensive way to overcome them until a better weapon comes along.
  • Unbreakable ArrowDMG: Great for archers to overcome resistance to damage from non-magical attacks, but it’s only one arrow so you really want to get a magic bow. Since the arrow can’t be broken, it’s weirdly useful for wedging doors and windows closed or open.
  • Walloping ArrowDMG: Great for archers to overcome resistance to damage from non-magical attacks, but the DC of 10 won’t be reliable and knocking foes prone makes it hard to hit them with ranged attacks which may hamper you and your allies.

Uncommon Magic Items

  • Ammunition, +1DMG: Single-use and expensive. Get a +X weapon instead, if you can.
  • Amulet of Proof against Detection and LocationDMG: Permanent Nondetection, similar to the spell. Combine this with Invisibility, and you can’t be detected by common countermeasures like See Invisibility.
  • Boomerang, +1DMG: Helpful if you need a thrown weapon occasionally, but you can’t use two-weapon fighting with it like you can with daggers, and if you hit you no longer have your magic weapon. Throwing mundane daggers is almost certainly more effective.
  • Boots of ElvenkindDMG: Helpful on any stealthy character, though not effective as a Cloak of Elvenkind. Combine with a Cloak of Elvenkind for maximum effect.
  • Bracers of ArcheryDMG: With only one attack per turn (usually), this won’t be effective enough to justify the item.
  • Broom of FlyingDMG: Easily overlooked, but one of the best ways to get flight for any character. It doesn’t require attunement, and has a fly speed of 50 feet, though many medium characters will exceed the 200 pound limit to reduce the speed to 30 feet, but even then 30 feet fly speed with no duration cap and requiring no action after speaking the command word is absolutely incredible. The only drawback is that you’re using the item’s speed rather than giving yourself a fly speed, so things that improve your speed won’t make the broom move faster, and you can’t Dash with the broom. Even so, I honestly can’t justify why this is only Uncommon considering how exceptionally good it is.
  • Cloak of ElvenkindDMG: Essential on any stealthy character. Creatures attempting to detect you suffer Disadvantage, and you gain Advantage on Stealth checks to avoid being seen, so you get two layers of protection against creatures detecting you.
  • Cloak of ProtectionDMG: Good on any character, but it requires Attunement and it’s not very interesting.
  • Eversmoking BottleDMG: A great way to escape, to hide, to create distractions, or any other number of things, the Eversmoking Bottle is a great tool for any rogue.
  • Eyes of Minute SeeingDMG: Excellent in dungeon crawls. Investigation is typically used for finding things like traps.
  • Eyes of the EagleDMG: Between this and possibly Expertise, it’s basically impossible for anything to sneak up on you without using magic.
  • Gloves of ThieveryDMG: Easily replaced by the Enhance Ability spell, but still helpful for stealthy characters.
  • Goggles of NightDMG: Crucial for races which don’t get Darkvision, especially if your party can’t cast the Darkvision spell for you.
  • Hat of DisguiseDMG: Great for social situations, but usually you can get by with mundane disguises or with a lower-rarity option like a Masquerade Tattoo.
  • Pearl of PowerDMG: Tempting for the Arcane Trickster.
  • Slippers of Spider ClimbingDMG: The next-best thing to flight. Walking up a wall has all the benefits of flying out of reach, making this an excellent option for ranged builds.
  • Stone of Good LuckDMG: Excellent on literally any character, but if you just want better defense a Cloak of Protection may be more effective. Stone of Good Luck shines if you’re heavily reliant on skills and ability checks, and note that ability checks include initiative rolls.
  • Weapon of WarningDMG: While it’s not as mathematically effective as a +1 weapon, being Attuned to a Weapon of Warning is still hugely beneficial for the Rogue even if you’re actually fighting with a different weapon. Assassins in particular will enjoy Advantage on Initiative rolls so that they can more reliably benefit from Assassinate.
  • Weapon, +1DMG: +1 to hit with your attacks improves the likelihood of delivering a Sneak Attack.
  • Winged BootsDMG: Excellent on its own, but Winged Boots are more limited in use than a broom of flying, and they require Attunement.

Rare Magic Items

  • Ammunition, +2DMG: Single-use and expensive. Get a +X weapon instead, if you can.
  • Amulet of HealthDMG: Setting your Constitution to 19 means that you don’t need to put Ability Score Increases into it unless you’re really certain that you want 20 Constitution. Less ASI’s into Constitution means more room for feats.
  • Armor of ResistanceDMG: Excellent, but unpredictable in most games since you can’t perfectly predict what sort of damage you’ll face. Fire and poison are safe choices.
  • Armor, +1DMG: +1 AC, no attunement. Nothing fancy, but very effective.
  • Cloak of DisplacementDMG: Among the best defensive items in the game. Taking damage from any source (spells, etc.) suppresses the effect temporarily, so make a point to kill anything that can damage you without an attack roll.
  • Cloak of the BatDMG: A Cloak of Elvenkind may be more effective for Stealth because it also imposes Disadvantage on Perception checks to detect you, but Cloak of the Bat isn’t limited to vision-based checks so it may be more broadly effective if your enemies can also hear or smell you (yes, that’s a thing). You can also use it to fly in dim light and darkness, though your hands are occupied (you need to hold the edges of the cloak) so flying in combat may be difficult.
  • Dagger of VenomDMG: Basically just a +1 dagger with a once-per-day poison. The poison is decent, but it’s not nearly enough to justify the difference in rarity. Get a +2 weapon instead.
  • FlametongueDMG: Mathematically the +2 bonus to attack rolls from a +2 weapon will be a more consistent improvement to your damage output (especially with the damge bonus from Sneak Attack), but a Flametongue shortsword or rapier is still really fun. The 2d6 damage is multiplied on critical hits, too, so assassin rogues might find it appealing.
  • Periapt of Proof Against PoisonDMG: Poison damage is very common across the full level range, so immunity to it is a significant improvement in your durability.
  • Ring of EvasionDMG: A great way to mitigate damage from AOE spells and things like breath weapons which can often be problems from front-line martial characters, especially if you’re not build around Dexterity.
  • Ring of ProtectionDMG: Cloak of Protection is lower rarity and has the same effect.
  • Ring of ResistanceDMG: A fine item in a vaccuum, but a Ring of Spell Storing full of Absorb Elements will be much more effective.
  • Ring of Spell StoringDMG: Fill it with Absorb Elements and Shield, and recharge it whenever possible and this is a spectacular defensive asset.
  • Shadowfell Brand TattooDMG: A Cloak of Elvenkind will technically be better at keeping you hidden because it also imposes Disadvantage on Perception checks to notice you, and the Shadowy Defense effect is partially redundant with Uncanny Dodge.
  • Sun BladeDMG: Basically a +2 rapier that deals radiant damage and does a bit more damage to undead. It’s not significantly better than a +2 rapier in the majority of cases. Radiant damage is great, but most creatures with resistance to weapon damage types are affected normally by magic weapons so the benefits of radiant damage compared to piercing or slashing damage from a magical wapon are minor. It works, but I’m not certain that it’s worth Attunement compared to a +2 weapon unless you can expect to face fiends and undead with some regularity.
  • Sword of WoundingDMG: Persistent damage that stacks with itself. It’s only 1d4 and only once per turn, but it stacks with itself and “once per turn” means that if you can attack again outside of your own turn (Opportunity Attacks, etc.) you can get additional dice very quickly.
  • Weapon, +2DMG: Mathematically spectacular. It’s difficult to beat the math here.
  • Wings of FlyingDMG: Broom of Flying is much better, lower rarity, and doesn’t require attunement.

Very Rare Magic Items

  • Absorbing TattooTCoE: Good, but too high rarity to devote to a single damage type. Get a Ring of Spell Storing and fill it with Absorb Elements.
  • Ammunition, +3DMG: Single-use and expensive. Get a +X weapon instead, if you can.
  • Animated ShieldDMG: Tempting for anyone not fighting with a one-handed weapon, but a Cloak of Protection is two rarities lower, works persistently, and arguably provides a better numeric bonus.
  • Armor, +2DMG: +2 AC, no attunement. Nothing fancy, but very effective.
  • Manual of Bodily HealthDMG: Permanent Constitution bonus and raises your cap by 2. Unless you’re using a magic item that fixes your Constitution as a specific score, this is excellent.
  • Manual of Quickness of ActionDMG: It’s difficult to find an item more broadly effective for the Rogue.
  • OathbowDMG: So cool, but so weak. Unless you’re attacking your sworn enemy, it’s just a magic bow with no benefit other than being chatty. Imagine using Action Surge and Haste and making 9 attacks in one turn and having the bow struggle to whisper “Swift defeat to my enemies” 9 times in six seconds.
  • Spellguard ShieldDMG: Basically only useful against spellcasters, but if you’re facing a spellcaster there are few better defenses.
  • Weapon, +3DMG: Mathematically spectacular. It’s difficult to beat the math here.

Legendary Magic Items

  • Armor, +3DMG: +3 AC, no attunement. Nothing fancy, but very effective. It feels underwhelming at this rarity, but the math if good.
  • Blood Fury TattooTCoE: The first ability provides a great damage boost which also heals you, and since it’s “extra damage” the damage is multiplied on a critical hit. The second ability provides a way to counterattack using your Reaction, and with Advantage on that attack it’s an easy and reliable boost to your damage output, and since you make the attack with Advantage it’s an easy way to get Sneak Attack outside of your turn. However, the attack uses your Reaction which means that you’re not using Uncanny Dodge so you need to weight that risk/reward calculation very carefully.
  • Cloak of InvisibilityDMG: Invisibility is extremely powerful in 5e. Note that this is just the invisible condition, not the spell spell Invisibility, so you can still attack or whatever while invisible.
  • Ioun Stone (Mastery)DMG: Proficiency Bonuses apply to a lot of things and a +1 bonus goes a long way. Attacks, saves, skills, etc. all benefit. For many characters, a Stone of Good Luck will be a better value, but rogues get more skill proficiencies than other classes, and at highl evels you’re proficient in three saves (assuming you didn’t get more from feats or something), so Ioun Stone (Mastery) applies to enough things that I think you can justify it over a Stone of Good Luck.
  • Luck BladeDMG: Bonuses to attacks and saves, a once per day reroll, and it can cast Wish a few times (maybe. 1d4-1 could be zero). Green if it can’t cast Wish.
  • Ring of InvisibilityDMG: Cloak of Invisibility and Ring of Invisibility are very similar, but there is some important nuance to understand. Ring of Invisibility can make you indefinitely invisible, allowing you to do anything except attack and cast spells without breaking your invisibility. Use a breath weapon, activate items (as long as doing so doesn’t make you cast a spell), steal things, use the Help action, pick locks, disarm traps, take long rests, etc. can all be done while totally invisible without limit. However, the second you roll initiative the Cloak of Invisibility becomes more powerful because its invisibility isn’t broken by you attacking or casting spells.
  • Ring of Spell TurningDMG: Given the choice, I would much rather haqve a Mantle of Spell Resistance simply because the Ring of Spell Turning doesn’t provide any protection against area effect spells. Otherwise, this is a really fun item, and if it provided Advantage on saves against area of effect spells it would shoot straight up to blue.
  • Ring of Three WishesDMG: Use this to do one of the things that risks permanently removing the ability to cast Wish, such as granting 10 creatures permanent resistance to once damage type. If you lose the ability to cast Wish, pass this off to another ally who will never be able to cast Wish by any other means. Repeat until the last charge is used.

    For more help with Wish, see my Practical Guide to Wish.

  • Scarab of ProtectionDMG: An upgrade from the Mantle of Spell Resistance, the Scarab of Protection adds a limited benefit against necromancy and undead creatures, and doesn’t take up your cloak slot, leaving you free to take items like a Cloak of Protection or Cloak of Invisibility instead.

Example Rogue Build – Lightfoot Halfling Rogue (Thief)

Corrie Edgecliff the Lightfoot Halfling Thief

Though her movements are lively and quick, the halfling’s green eyes give you a look that’s all business. Her leather armor, softened with some sort of oil to keep a free range of movement, has more than a few pouches built into it, the right size and shape to hold particulars such as a vial of acid, a bag of ball bearings, or a handful of iron door spikes. Though you cannot see any weapons, you would wager a dragon’s hoard that she has at least three daggers and a blowgun concealed on her person, if not more.

— Boxed text provided by dScryb (affiliate link)

This is a “Staple Build”. This build is simple, and relies on options from the SRD and the Basic Rules wherever possible. If you need a functional build with nothing fancy or complicated, this is a great place to start.

The Lightfoot Halfling Thief is, in my opinion, the most iconic example of the Rogue. My opinion may be biased by my 3rd-edition roots, in which Lidda the Halfling Rogue was the iconic example of the class, but the concept of a halfling sneaking around stealing things dates all the way back to The Hobbit.

With the options available to us in the Basic Rules and the SRD, we’ll build our rogue as a combination Face, Scout, and Striker. These are the Rogue’s typical roles, and this build can cover all the bases reasonably well at the same time. Our Face and Scout emphasis will be a balance because each will consume our limited choices of skill proficiencies and Expertise. I’ll present some suggested options, but I encourage you to customize your build to suit your tastes.

I’ll note two DPR entries below: One for a single attack, and one for two-weapon fighting. While the additional attack itself does a miniscule amount of additional damage, the additional opportunity to deal Sneak Attack damage is a massive mathematical advantage that only grows as you gain levels.

Abilities

We will use the ability scores below. They’re almost identical to the suggested ability scores presented above for “most rogues”, but they’re tweaked a little bit to take advantage of the Lightfoot Halfling’s ability score increases so that we can get as much out of our build as possible.

 BaseIncreased
Str88
Dex1416
Con1414
Int1212
Wis1212
Cha1314

Race

Lightfoot Halfling. Dexterity and Charisma is likely the best ability score spread we can get for a thief, and the Lightfoot Halfling’s other racial traits offer a bunch of other useful tricks.

Skills and Tools

Rogues get more skills at first level than any other class, and they also get Expertise immediately. You also get Thieves’ Tools proficiency on top of the rest.

  • Perception
  • Persuasion
  • Sleight of Hand
  • Stealth

If you choose the Criminal background, you’ll get a redundant Stealth proficiency which you can trade for Insight or Intimidation. If you choose the Noble background you’ll get a redundant Persuasion proficiency which you can trade for Deception.

For Expertise, I recommend Perception and Stealth. Other skills are appealing, but you’re more likely to die because of a failed Perception or Stealth check than for failed Persuasion check. At 6th level you’ll get Expertise in two more skills, at which point you should consider skills which fit your campaign. If you’re doing a lot of stealing, consider Sleight of Hand and Thieves’ Tools. If you’re doing a lot socially acceptable things, consider Deception and Persuasion.

Background

Criminal is the obvious choice here, so we’ll pick Criminal. However, it might not be the best choice among those available to use. Rogue grants Thieves’ Tools proficiency automatically, so Criminal’s tool proficiency is redundant. Under the rules for backgrounds, you can replace a redundant proficiency with one of the same type, but what other set of tools do you want? If you want proficiency in something like Healer’s Kit or Herbalism Kit, Criminal is great. If you can’t think of a second set of tools, look for other background options.

If Criminal doesn’t work for you, consider Noble. History proficiency isn’t a great choice for our low-Intelligence build, but you get Persuasion, a gaming set, and a language, and Position of Privilege is a great way to roleplay yourself into places with nice things to steal.

Feats

Rogues get one more ability score improvement than most classes, and you only need to bring on ability score (Dexterity) to 20 to be successful, so there is a lot of room for you to pick up feats if you’re willing to deviate from the Basic Rules and the SRD. If you’re new to the game, consider simple feats like Skilled or Resilient. If you want to dabble in magic, consider Magic Initiate and take a look at the Spells section above.

Levels

LevelFeat(s) and FeaturesNotes and Tactics
1
  • Expertise
    • Perception
    • Stealth
  • Sneak Attack 1d6
  • Thieves’ Cant

For your starting equipment, take a shortsword, a short bow, any of the pack options, leather armor, two daggers, and theives’ tools.

At first level you already have most of what makes you a decent rogue. Sneak Attack is still picking up steam, but 1d6 is a big chunk of damage at this level, so do everything you can to get it.

In combat, you can either fight at range or jump into melee as the situation warrants. If you’re fighting at range, you’re totally dependent on an ally to be adjacent to your target, so make sure to communicate with your party’s front-line characters. If you’re fighting in melee, grab your short sword and a dagger and practice two-weapon fighting. If an enemy is just out of reach, throw your dagger; you have two for a reason.

One Attack: Dagger 1d4+3 with +1d6 Sneak Attack (DPR 5.6)

Two-Weapon Fighting: Dagger 1d4+3 and Dagger 1d4 with +1d6 Sneak Attack (DPR 8.1)

2
  • Cunning Action

Cunning Action shakes up your action economy in combat. Now you need think a little more about how to use your Bonus Action.

If you’re fighting at range, find cover (potentially behind a medium-sized ally) to hide behind. Each turn you should attack with your bow then use Cunning Action to hide.

If you’re fighting in melee, hit-and-run tactics are the ideal. Attack with your short sword, then use Cunning Action to Disengage and move away safely. If you miss, consider using your bonus action to attack with your dagger to get a second chance at dealing Sneak Attack. If you hit and kill your target, consider using Cunning Action to Dash and put some extra distance between you and anything dangerous.

One Attack: Dagger 1d4+3 with +1d6 Sneak Attack (DPR 5.6)

Two-Weapon Fighting: Dagger 1d4+3 and Dagger 1d4 with +1d6 Sneak Attack (DPR 8.1)

3
  • Sneak Attack 2d6
  • Roguish Archetype (Thief)
  • Fast Hands

At 2d6, yor Sneak Attack damge should roughly match the total damage from your weapons and your Dexterity bonus.

Fast Hands is easy to overlook, but the “Use an Item” action covers a lot of great options. Ball Bearings, Caltrops, Holy Water, and some magic items are all activated using the Use An Item action normally. You can do all of those things as a Bonus Action, so you could attack, throw down some caltrops, then move to safety all in one turn.

One Attack: Dagger 1d4+3 with +2d6 Sneak Attack (DPR 7.8)

Two-Weapon Fighting: Dagger 1d4+3 and Dagger 1d4 with +2d6 Sneak Attack (DPR 11.2)

4
  • Ability Score Improvement (Dexterity 16 -> 18)

A numerical increase to the vast majority of what you do feels very satisfying.

One Attack: Dagger 1d4+4 with +2d6 Sneak Attack (DPR 8.4)

Two-Weapon Fighting: Dagger 1d4+4 and Dagger 1d4 with +2d6 Sneak Attack (DPR 11.8)

5
  • Sneak Attack 3d6
  • Uncanny Dodge

More Sneak Attack damage is always welcome, but it doesn’t change our tactics in any way. Uncanny Dodge is the interesting gain here. Since it uses your Reaction, it won’t cut into your normal activity during your turn. In some cases you might risk provoking an Opportunity Attack knowing that you can use Uncanny Dodge to reduce the damage if you get hit. If you decide to stay still, you can mitigate some damage with Uncanny Dodge but remember that you only get one Reaction per round so creatures with multiple attacks may be a problem.

One Attack: Dagger 1d4+4 with +3d6 Sneak Attack (DPR 10.6)

Two-Weapon Fighting: Dagger 1d4+4 and Dagger 1d4 with +3d6 Sneak Attack (DPR 14.9)

6
  • Expertise
    • Sleight of Hand
    • Thieves’ Tools

Fast Fingers allows you to perform Sleight of Hand checks and to use your Thieves’ Tools for certain tasks as a bonus action. Expertise will make you better at these tasks. I’m not entirely sure under what circumstances you would do this, but you’re now really good at picking pockets in the middle of a fight.

One Attack: Dagger 1d4+4 with +3d6 Sneak Attack (DPR 10.6)

Two-Weapon Fighting: Dagger 1d4+4 and Dagger 1d4 with +3d6 Sneak Attack (DPR 14.9)

7
  • Sneak Attack 4d6
  • Evasion

Evasion makes many AOE effects, including breath weapons and fireballs, less threatening. Your Dexterity saves should be excellent, so you’ll frequently be able to fully avoid damage from applicable effects.

One Attack: Dagger 1d4+4 with +4d6 Sneak Attack (DPR 12.8)

Two-Weapon Fighting: Dagger 1d4+4 and Dagger 1d4 with +4d6 Sneak Attack (DPR 18.0)

8
  • Ability Score Improvement (Dexterity 18 -> 20)

This brings our Dexterity to the maximum.

One Attack: Dagger 1d4+5 with +4d6 Sneak Attack (DPR 13.4)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +4d6 Sneak Attack (DPR 18.6)

9
  • Sneak Attack 5d6
  • Supreme Sneak

Between Expertise and your 20 Dexterity, you have a +13 bonus on Dexterity (Stealth) checks, and now you have a way to get Advantage guaranteed. You’re borderline undetectable.

One Attack: Dagger 1d4+5 with +5d6 Sneak Attack (DPR 15.7)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +5d6 Sneak Attack (DPR 21.7)

10
  • Ability Score Improvement (Charisma 14 -> 16)

At this level we’re getting an Ability Score Increase that we don’t strictly need. I’ve suggested Charisma, but if you’re doing more fighting than talking you may want Constitution instead.

One Attack: Dagger 1d4+5 with +5d6 Sneak Attack (DPR 15.7)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +5d6 Sneak Attack (DPR 21.7)

11
  • Sneak Attack 6d6
  • Reliable Talent

Reliable Talent makes you really good at skills. You’re already really good, but this removes the possibility of horribly low rolls. It raises the average d20 roll from 10.5 to 12.75, and a +2.25 bonus on all your skills is huge.

One Attack: Dagger 1d4+5 with +6d6 Sneak Attack (DPR 17.9)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +6d6 Sneak Attack (DPR 24.9)

12
  • Ability Score Improvement (Charisma 16 -> 18)

More Constitution or Charisma. Or a feat. Your choice.

One Attack: Dagger 1d4+5 with +6d6 Sneak Attack (DPR 17.9)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +6d6 Sneak Attack (DPR 24.9)

13
  • Sneak Attack 7d6
  • Use Magic Device

Use Magic Device only matters in campaigns with magic items, which is odd because 5e so rarely assumes that you use magic items. There are very few magic items with restrictions which this will bypass, but you’re going to feel really special if you find one and get to break the rules to use it.

One Attack: Dagger 1d4+5 with +7d6 Sneak Attack (DPR 20.1)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +7d6 Sneak Attack (DPR 27.9)

14
  • Blindsense

Invisibility becomes more common at high levels, and unless you have a spellcaster handy it’s often very difficult to deal with. This helps quite a bit, but remember tha you’ll still have Disadvantage to attack the creature because you can’t see it.

One Attack: Dagger 1d4+5 with +7d6 Sneak Attack (DPR 20.1)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +7d6 Sneak Attack (DPR 27.9)

15
  • Sneak Attack 8d6
  • Slippery Mind

More saving throw proficiencies is always excellent.

One Attack: Dagger 1d4+5 with +8d6 Sneak Attack (DPR 22.3)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +8d6 Sneak Attack (DPR 30.9)

16
  • Ability Score Improvement (Charisma 18 -> 20)

Still more Constitution or Charisma.

One Attack: Dagger 1d4+5 with +8d6 Sneak Attack (DPR 22.3)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +8d6 Sneak Attack (DPR 30.9)

17
  • Sneak Attack 9d6
  • Thief’s Reflexes

Two turns in the first round of combat means two opportunities to deal a Sneak Attack early in the fight. Target foes which you can eliminate quickly so that your party starts the fight with an early advantage.

One Attack: Dagger 1d4+5 with +9d6 Sneak Attack (DPR 24.5)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +9d6 Sneak Attack (DPR 34.0)

18
  • Elusive

Short of Pack Tactics, most enemies don’t have easy ways to gain Advantage against players, so this won’t matter frequently, but the few times it comes up you’ll be glad to have it.

One Attack: Dagger 1d4+5 with +9d6 Sneak Attack (DPR 24.5)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +9d6 Sneak Attack (DPR 34.0)

19
  • Sneak Attack 10d6
  • Ability Score Improvement (Constitution 14 -> 16)

More damage, more ability scores.

One Attack: Dagger 1d4+5 with +10d6 Sneak Attack (DPR 26.7)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +10d6 Sneak Attack (DPR 37.1)

20
  • Stroke of Luck

Stroke of Luck doesn’t apply to saving throws, so there’s little reason to sit on it. Use it early, use it often.

One Attack: Dagger 1d4+5 with +10d6 Sneak Attack (DPR 26.7)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +10d6 Sneak Attack (DPR 37.1)